BE512654A - - Google Patents
Info
- Publication number
- BE512654A BE512654A BE512654DA BE512654A BE 512654 A BE512654 A BE 512654A BE 512654D A BE512654D A BE 512654DA BE 512654 A BE512654 A BE 512654A
- Authority
- BE
- Belgium
- Prior art keywords
- isoquinoline
- compounds
- hydrazine
- salts
- group
- Prior art date
Links
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- 150000002537 isoquinolines Chemical class 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- IOOUWJDACLDFNP-UHFFFAOYSA-N isoquinolin-1-ylhydrazine Chemical compound C1=CC=C2C(NN)=NC=CC2=C1 IOOUWJDACLDFNP-UHFFFAOYSA-N 0.000 claims description 6
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 4
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- 230000009466 transformation Effects 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 description 7
- 239000000047 product Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- -1 carbonyl organic compounds Chemical class 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- MSQCQINLJMEVNJ-UHFFFAOYSA-N 1-chloroisoquinoline Chemical compound C1=CC=C2C(Cl)=NC=CC2=C1 MSQCQINLJMEVNJ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- NRBSVPXPMBQUGX-UHFFFAOYSA-N 1,7-dichloroisoquinoline Chemical compound C1=CN=C(Cl)C2=CC(Cl)=CC=C21 NRBSVPXPMBQUGX-UHFFFAOYSA-N 0.000 description 1
- SSBMOLGNIQJGPF-UHFFFAOYSA-N 1-chloro-7-methoxyisoquinoline Chemical compound C1=CN=C(Cl)C2=CC(OC)=CC=C21 SSBMOLGNIQJGPF-UHFFFAOYSA-N 0.000 description 1
- FBQJSTRRHBTMMQ-UHFFFAOYSA-N 1-chloro-7-methylisoquinoline Chemical compound C1=CN=C(Cl)C2=CC(C)=CC=C21 FBQJSTRRHBTMMQ-UHFFFAOYSA-N 0.000 description 1
- JBOILZFFYWYWNY-UHFFFAOYSA-N 1-piperidin-1-ylisoquinoline Chemical compound C1CCCCN1C1=NC=CC2=CC=CC=C12 JBOILZFFYWYWNY-UHFFFAOYSA-N 0.000 description 1
- RSWLKWLWFHJIFZ-UHFFFAOYSA-N C1=NC=CC2=CC=CC=C12.NN Chemical class C1=NC=CC2=CC=CC=C12.NN RSWLKWLWFHJIFZ-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000001034 aminogenic effect Effects 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 150000001261 hydroxy acids Chemical class 0.000 description 1
- OSILBMSORKFRTB-UHFFFAOYSA-N isoquinolin-1-amine Chemical compound C1=CC=C2C(N)=NC=CC2=C1 OSILBMSORKFRTB-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- MOYDPHICGXAWEG-UHFFFAOYSA-N n-butylisoquinolin-1-amine Chemical compound C1=CC=C2C(NCCCC)=NC=CC2=C1 MOYDPHICGXAWEG-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE512654A true BE512654A (enrdf_load_stackoverflow) |
Family
ID=151031
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE512654D BE512654A (enrdf_load_stackoverflow) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE512654A (enrdf_load_stackoverflow) |
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0
- BE BE512654D patent/BE512654A/fr unknown